Total Synthesis of (−)-Colchicine by an Oxyallyl [4+3] Cycloaddition

Lee, Jae Chol; Kun, Jin

doi:10.1016/s0040-4020(00)00862-0

Cited by 61 publications

(18 citation statements)

References 17 publications

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“…A recent paper reports the synthesis of a fragment of colchicine by the acylation of zinc reagent 5a (Scheme 17). 61 The low yield in this reaction is a reflection of the relatively unreactive electrophile, and higher yields were obtained in a model reaction with benzoyl chloride (52-65%).…”

Section: Scheme 14mentioning

confidence: 86%

Development and Applications of Amino Acid Derived Organometallics

Rilatt¹,

Caggiano²,

Jackson³

2005

Synlett

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This Account describes the discovery and development of a family of organometallic reagents derived from naturally occurring a-amino acids that have found widespread use in the stereocontrolled synthesis of non-natural analogues of proteinogenic amino acids. The general approach that we have taken involves the conversion of the side chain of enantiomerically pure naturally occurring amino acids, such as serine, aspartic acid and glutamic acid, into the corresponding primary alkyl iodide, followed by conversion into the corresponding organozinc reagents. Subsequent palladium-or copper-catalysed reactions of these reagents allow the synthesis of a wide variety of functionalised a-, b-and g-amino acid derivatives, without loss of stereochemical integrity. Insights gained from spectroscopic and kinetic studies into the stability of functionalised organozinc reagents are included.

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Section: Scheme 14mentioning

confidence: 86%

Development and Applications of Amino Acid Derived Organometallics

Rilatt¹,

Caggiano²,

Jackson³

2005

Synlett

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“…A novel total chiral synthesis of (-)-colchicine by Cha and coworkers, reported in 1998 [3] is delineated with fairly detailed experimental conditions and reagents in Fig. 24.4.…”

Section: Chiral Synthesis Of (-)-Colchicinementioning

confidence: 99%

“…MS [18,19] [4]. Their assignments were not given earlier [4]. The assignments of some quaternary carbons having similar δ-values, e.g., C3, C7a, and C1 (a) or C12a and C4a (b), and some primary carbons, e.g., C13 and C14 or C15 and C18, are arbitrary and interchangeable.…”

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confidence: 99%

Colchicine, A Phenylethylisoquinoline Alkaloid Derived from L-Tyrosine

Talapatra

2014

Chemistry of Plant Natural Products

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“…However, theoretical calculations support an alternative stepwise mechanism for certain examples [174,177]. An example of employing such a reaction as the key step in the total synthesis of colchicine is shown in Scheme 6.92 [178]. Thus, coupling of the highly substituted furan 199 with the oxyallyl cation generated from silyl enol ether 200 produces the desired endo-adduct 201 as a single isomer.…”

Section: Reactions With Radical Reagentsmentioning

confidence: 99%